DE2064471C2 - Verfahren zur Herstellung von Aldehyden durch Hydroformylierung - Google Patents
Verfahren zur Herstellung von Aldehyden durch HydroformylierungInfo
- Publication number
- DE2064471C2 DE2064471C2 DE2064471A DE2064471A DE2064471C2 DE 2064471 C2 DE2064471 C2 DE 2064471C2 DE 2064471 A DE2064471 A DE 2064471A DE 2064471 A DE2064471 A DE 2064471A DE 2064471 C2 DE2064471 C2 DE 2064471C2
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- product
- complex
- hydroformylation
- rhodium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 22
- 230000008569 process Effects 0.000 title claims description 12
- 150000001299 aldehydes Chemical class 0.000 title claims description 8
- 238000007037 hydroformylation reaction Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003054 catalyst Substances 0.000 claims description 28
- 239000003446 ligand Substances 0.000 claims description 13
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 13
- 239000012429 reaction media Substances 0.000 claims description 11
- 239000010948 rhodium Substances 0.000 claims description 11
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229910052703 rhodium Inorganic materials 0.000 claims description 7
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 238000006561 solvent free reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 19
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 230000000087 stabilizing effect Effects 0.000 description 6
- -1 hydridocarbonyl Chemical group 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- IETKMTGYQIVLRF-UHFFFAOYSA-N carbon monoxide;rhodium;triphenylphosphane Chemical compound [Rh].[O+]#[C-].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 IETKMTGYQIVLRF-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 238000003822 preparative gas chromatography Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000282979 Alces alces Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- WUOIAOOSKMHJOV-UHFFFAOYSA-N ethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC)C1=CC=CC=C1 WUOIAOOSKMHJOV-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
- C07C27/20—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxo-reaction
- C07C27/22—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxo-reaction with the use of catalysts which are specific for this process
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/24—Phosphines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB6350369 | 1969-12-31 | ||
| GB2493370*[A GB1338225A (en) | 1969-12-31 | 1970-05-22 | Catalytic reactions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2064471A1 DE2064471A1 (de) | 1971-07-08 |
| DE2064471C2 true DE2064471C2 (de) | 1985-08-22 |
Family
ID=26257394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2064471A Expired DE2064471C2 (de) | 1969-12-31 | 1970-12-30 | Verfahren zur Herstellung von Aldehyden durch Hydroformylierung |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5317573B1 (enrdf_load_stackoverflow) |
| BE (1) | BE761031A (enrdf_load_stackoverflow) |
| CA (1) | CA987679A (enrdf_load_stackoverflow) |
| DE (1) | DE2064471C2 (enrdf_load_stackoverflow) |
| ES (1) | ES386876A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2072146B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1338225A (enrdf_load_stackoverflow) |
| NL (1) | NL172442C (enrdf_load_stackoverflow) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA78146B (en) * | 1977-01-25 | 1978-12-27 | Union Carbide Corp | Improved hydroformylation process |
| GB2000124B (en) * | 1977-06-21 | 1982-03-24 | Johnson Matthey Co Ltd | Catalysts |
| CA1104587A (en) * | 1977-06-21 | 1981-07-07 | Peter J. Davidson | Catalytic hydroformylation of internal olefins |
| US4288634A (en) * | 1978-04-10 | 1981-09-08 | Toa Nenryo Kogyo Kabushiki Kaisha | Novel rhodium compounds and process for producing the same |
| JPS5849534B2 (ja) * | 1979-04-06 | 1983-11-05 | 東亜燃料工業株式会社 | アルデヒドの製造方法 |
| US4260828A (en) * | 1980-04-16 | 1981-04-07 | Union Carbide Corporation | Hydroformylation process |
| EP0096987B1 (en) * | 1982-06-11 | 1985-11-13 | DAVY McKEE (LONDON) LIMITED | Hydroformylation process |
| ATE26696T1 (de) * | 1982-06-11 | 1987-05-15 | Davy Mckee London | Hydroformylierungsverfahren. |
| JPS59196452U (ja) * | 1983-06-14 | 1984-12-27 | 楠神 富生 | 不祝儀袋 |
| JPS606630A (ja) * | 1983-06-24 | 1985-01-14 | Kuraray Co Ltd | アリルアルコ−ルの連続ヒドロホルミル化方法 |
| US5012008A (en) * | 1990-01-08 | 1991-04-30 | Drago Russell S | Supported amorphous phase heterogeneous catalysts for biphasic hydroformylation |
| CN104045532B (zh) | 2013-03-15 | 2018-05-25 | 陶氏技术投资有限责任公司 | 加氢甲酰化方法 |
| JP6908602B2 (ja) | 2015-11-10 | 2021-07-28 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | アルデヒドの生成プロセス |
| CN108698962B (zh) | 2016-02-11 | 2022-02-25 | 陶氏技术投资有限责任公司 | 将烯烃转化成醇、醚或其组合的方法 |
| TW201840362A (zh) | 2016-11-08 | 2018-11-16 | 美商陶氏科技投資有限公司 | 使去活化的氫甲醯化催化劑溶液再生的方法 |
| TWI758353B (zh) | 2016-11-08 | 2022-03-21 | 美商陶氏科技投資有限公司 | 使去活化的氫甲醯化催化劑溶液再生的方法 |
| TW201840363A (zh) | 2016-11-08 | 2018-11-16 | 美商陶氏科技投資有限公司 | 處理氫甲醯化催化劑溶液之方法 |
| KR20250057144A (ko) | 2018-05-30 | 2025-04-28 | 다우 테크놀로지 인베스트먼츠 엘엘씨. | 하이드로포밀화 공정에서 촉매의 탈활성화를 느리게 하고/하거나 테트라포스핀 리간드 사용을 느리게 하는 방법 |
| WO2019231611A1 (en) | 2018-05-30 | 2019-12-05 | Dow Technology Investments Llc | Methods of controlling hydroformylation processes |
| EP3801898A1 (en) | 2018-05-30 | 2021-04-14 | Dow Technology Investments LLC | Catalyst composition comprising the combination of a monophopsphine, a tetraphosphine ligand and a hydroformylation process using it |
| KR20240108441A (ko) | 2021-11-11 | 2024-07-09 | 다우 테크놀로지 인베스트먼츠 엘엘씨. | 히드로포르밀화 공정으로부터의 로듐의 회수 공정 |
| CN120282943A (zh) | 2022-12-13 | 2025-07-08 | 陶氏技术投资有限责任公司 | 通过利用降解产物使多膦使用最小化的方法 |
| WO2025006020A1 (en) | 2023-06-26 | 2025-01-02 | Dow Technology Investments Llc | Methods of controlling hydroformylation processes |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE627365A (enrdf_load_stackoverflow) * | 1962-01-23 | |||
| GB1219763A (en) * | 1967-02-02 | 1971-01-20 | Johnson Matthey & Company | Improvements in catalytic hydrogenation or hydroformylation |
| US3487112A (en) * | 1967-04-27 | 1969-12-30 | Monsanto Co | Vapor phase hydroformylation process |
| US3527809A (en) * | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| DE1939322B2 (de) * | 1968-08-02 | 1981-02-26 | Johnson, Matthey & Co., Ltd., London | Verfahren zur Hydroformylierung olefinisch ungesättigter Verbindungen |
-
1970
- 1970-05-22 GB GB2493370*[A patent/GB1338225A/en not_active Expired
- 1970-12-28 JP JP12515270A patent/JPS5317573B1/ja active Pending
- 1970-12-29 NL NLAANVRAGE7018912,A patent/NL172442C/xx not_active IP Right Cessation
- 1970-12-29 ES ES386876A patent/ES386876A1/es not_active Expired
- 1970-12-30 DE DE2064471A patent/DE2064471C2/de not_active Expired
- 1970-12-30 BE BE761031A patent/BE761031A/xx not_active IP Right Cessation
- 1970-12-30 FR FR707047204A patent/FR2072146B1/fr not_active Expired
- 1970-12-30 CA CA101,763A patent/CA987679A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL172442B (nl) | 1983-04-05 |
| DE2064471A1 (de) | 1971-07-08 |
| GB1338225A (en) | 1973-11-21 |
| BE761031A (fr) | 1971-05-27 |
| JPS5317573B1 (enrdf_load_stackoverflow) | 1978-06-09 |
| NL172442C (nl) | 1983-09-01 |
| ES386876A1 (es) | 1973-12-01 |
| FR2072146B1 (enrdf_load_stackoverflow) | 1973-02-02 |
| CA987679A (en) | 1976-04-20 |
| NL7018912A (enrdf_load_stackoverflow) | 1971-07-02 |
| FR2072146A1 (enrdf_load_stackoverflow) | 1971-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8331 | Complete revocation |